Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (6): 1613-1622.DOI: 10.6023/cjoc201901021 Previous Articles     Next Articles

Articles

光诱导原子经济的迭代型末端炔烃氢三氟甲基化和远程C(sp3)-H键官能团化

刘涛a, 屈川华a, 谢劲a, 朱成建a,b   

  1. a 南京大学化学化工学院 南京 210023;
    b 金属有机化学国家重点实验室 上海有机化学研究所 上海 200032
  • 收稿日期:2019-01-16 修回日期:2019-01-24 出版日期:2019-06-25 发布日期:2019-02-19
  • 通讯作者: 谢劲, 朱成建 E-mail:xie@nju.edu.cn;cjzhu@nju.edu.cn
  • 基金资助:

    国家自然科学基金(Nos.21702098,21732003,21672099)、青年千人资助项目和和本科有机化学实验课程开放课题资助项目.

Photoinduced Atom-Economical Iterative Hydrotrifluoromethylation of Terminal Alkynes and Remote C(sp3)-H Functionalization

Liu Taoa, Qu Chuanhuaa, Xie Jina, Zhu Chengjiana,b   

  1. a School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023;
    b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Shanghai 200032
  • Received:2019-01-16 Revised:2019-01-24 Online:2019-06-25 Published:2019-02-19
  • Contact: 10.6023/cjoc201901021 E-mail:xie@nju.edu.cn;cjzhu@nju.edu.cn
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21702098, 21732003, 21672099), the 1000-Youth Talents Plan and the Open Training Program of Undergraduate Organic Experiment Course.

Trifluoromethylation using Togni reagents usually releases one equivalent of iodobenzoats as wasteful byproducts. A visible-light-mediated, atom-and step-economical hydrotrifluoromethylation of aromatic alkynes and remote benzoyl-oxylation of α-C(sp3)-H bond of ether with Togni reagent as a bifunctional reagent by means of hydrogen atom transfer strategy was disclosed. The combination of two organic transformations into one reaction not only brings 100% atom economy but also addresses the challenge of stereoselective hydrotrifluoromethylation of aromatic alkynes. This unprecedented protocol offers an important access to a wide range of highly functionalized CF3-containing alkenes with great potential for post-modification.

Key words: hydrotrifluoromethylation, visible light, atom-economical, hydrogen transfer